Ethanedione, diphenyl-

Formula: C₁₄H₁₀O₂
Molecular weight: 210.2280
IUPAC Standard InChI: InChI=1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H
IUPAC Standard InChIKey: WURBFLDFSFBTLW-UHFFFAOYSA-N
CAS Registry Number: 134-81-6
Chemical structure:
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Other names: Benzil; Bibenzoyl; Dibenzoyl; Diphenyl-α,β-diketone; Diphenylethanedione; Diphenylglyoxal; 1,2-Diphenylethane-1,2-dione; 1,2-Diphenylethanedione; Glyoxal, diphenyl-; Wy 20910; 1,2-Ethanedione, 1,2-diphenyl-; NSC 220315
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
S°_gas	114.77	cal/mol*K	N/A	Dworkin A., 1983	The value of 428.1 J/molK was obtained for the third-law entropy value at 298.15 K if other enthalpy of sublimation of benzil was used. However, statistical values of S(298.15 K) calculated by author [ Dworkin A., 1983] for different molecular models (382.3 and 405.3 J/molK) are considerably less than the calorimetric values.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-36.80	kcal/mol	Ccb	Parks and Mosher, 1962	ALS
Δ_fH°_solid	-42.7	kcal/mol	Ccb	Springall and White, 1954	ALS
Δ_fH°_solid	33.1	kcal/mol	Ccb	Landrieu, 1906	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1621.5 ± 0.7	kcal/mol	Ccb	Parks and Mosher, 1962	Corresponding Δ_fHº_solid = -36.78 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1615.6 ± 0.8	kcal/mol	Ccb	Springall and White, 1954	Corresponding Δ_fHº_solid = -42.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1621.6	kcal/mol	Ccb	Barker, 1925	Author was aware that data differs from previously reported values; Corresponding Δ_fHº_solid = -36.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1632.1	kcal/mol	Ccb	Landrieu, 1906	Corresponding Δ_fHº_solid = -26.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	69.809	cal/mol*K	N/A	Dworkin A., 1983	DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
58.72	298.15	Dworkin A., 1983	T = 15 to 300 K.; DH

Gas phase ion energetics data

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Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.68 ± 0.05	PI	Polevoi, Matyuk, et al., 1987	LBLHLM
8.72	EI	Elder, Beynon, et al., 1976	LLK
8.86 ± 0.15	EI	Scheppele, Mitchum, et al., 1973	LLK
8.78 ± 0.05	EI	Natalis and Franklin, 1965	RDSH
8.9 ± 0.05	PE	McAlduff and Bunbury, 1979	Vertical value; LLK
9.1	PE	Arnett, Newkome, et al., 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₅⁺	15.1 ± 0.2	?	EI	Natalis and Franklin, 1965	RDSH
C₇H₅O⁺	9.43 ± 0.05	C₆H₅CO	PI	Polevoi, Matyuk, et al., 1987	LBLHLM
C₇H₅O⁺	9.64	C₆H₅CO	EI	Elder, Beynon, et al., 1976	LLK
C₇H₅O⁺	9.70 ± 0.05	?	EI	Natalis and Franklin, 1965	RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Dworkin A., 1983
Dworkin A., Heat capacity, phase transition, and thermodynamic properties of benzil, J. Chem. Thermodyn., 1983, 15, 1029-1035. [all data]

Parks and Mosher, 1962
Parks, G.S.; Mosher, H.P., Heats of combustion and formation of seven organic compounds containing oxygen, J. Chem. Phys., 1962, 37, 919-920. [all data]

Springall and White, 1954
Springall, H.D.; White, T.R., Heats of combustion and molecular structure. Part II. The mean bond energy term for the carbonyl system in certain ketones, J. Chem. Soc., 1954, 2765-27. [all data]

Landrieu, 1906
Landrieu, M.Ph., Thermochimie des hydrazones et des osazones, des dicetones-α et des sucres reducteurs, Compt. Rend., 1906, 140, 580-582. [all data]

Barker, 1925
Barker, M.F., Calorific value and constitution, J. Phys. Chem., 1925, 29, 1345-1363. [all data]

Polevoi, Matyuk, et al., 1987
Polevoi, A.V.; Matyuk, V.M.; Grigor'eva, G.A.; Potapov, V.K., Formation of intermediate products during the resonance stepwise polarization of dibenzyl ketone and benzil molecules, Russ. J. Phys. Chem., 1987, 21, 12. [all data]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Scheppele, Mitchum, et al., 1973
Scheppele, S.E.; Mitchum, R.K.; Kinneberg, K.F.; Meisels, G.G.; Emmel, R.H., Internal energy distributions and the fragmentation of gaseous organic ions. Dissociation of ions produced by electron impact on 4-methylbenzil, J. Am. Chem. Soc., 1973, 95, 5105. [all data]

Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L., Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. II. Diphenylcarbonyls and ethers, J. Phys. Chem., 1965, 69, 2943. [all data]

McAlduff and Bunbury, 1979
McAlduff, E.J.; Bunbury, D.L., Photoelectron spectra of some aromatic mono-and di-ketones, J. Electron Spectrosc. Relat. Phenom., 1979, 17, 81. [all data]

Arnett, Newkome, et al., 1974
Arnett, J.F.; Newkome, G.; Mattice, W.L.; McGlynn, S.P., Excited electronic states of the α-dicarbonyls, J. Am. Chem. Soc., 1974, 96, 4385. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,solid	Constant pressure heat capacity of solid
S°_gas	Entropy of gas at standard conditions
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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